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Chemical Compound Review

CHEMBL387744     N'-(phenylcarbonyl)-N-tert- butyl...

Synonyms: AG-D-31194, SureCN1538531, ACMC-20mftc, CHEBI:38457, MS-1114, ...
 
 
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Disease relevance of RH 5849

  • On the other hand, RH-5849 showed no acute toxicity to tadpoles during the 96 h exposure even it was saturated in the test solutions [1].
 

High impact information on RH 5849

 

Chemical compound and disease context of RH 5849

  • While in toxicity assays 20E was ineffective, most likely due to rapid metabolism, it was more potent than RH-5849 but less so than RH-5992 and RH-2485 in imaginal disc assays [5].
  • We conclude that RH-5849 does not mimic makisterone-A, as is the case with ecdysone, and that toxicity is mediated instead through non-endocrine targets in this insect species [6].
 

Biological context of RH 5849

  • Assessing the genotoxicity of imidacloprid and RH-5849 in human peripheral blood lymphocytes in vitro with comet assay and cytogenetic tests [7].
  • For bilaterally applied RH-5849, the concentration needed for 50% block (IC50) was 79 +/- 6 microM (mean +/- SEM, n = 3), with a Hill coefficient near 2 [8].
  • DNA damage scores increased with the exposure levels of both pesticides, and linear dose-effect relationships were observed for both imidacloprid (r2=0.98) and RH-5849 (r2=0.92) [7].
  • In addition, RH-5849 halted the larval and pupal growth, where the untreated pupae were generally heavier than those produced from treated larvae [9].
  • In regard to the fecundity and egg viability, RH-5849 induced a cessation of oviposition in females produced from 1-day-old and from 4-day-old larvae fed on diets treated with 160 and 200 ppm, respectively [9].
 

Anatomical context of RH 5849

  • In vitro effect of nonsteroidal ecdysone agonist RH 5849 on fat body acid phosphatase activity in rice moth, Corcyra cephalonica (Insecta) [10].
 

Associations of RH 5849 with other chemical compounds

  • Effect of bisacylhydrazine ecdysteroid mimics (RH-5849 and RH-5992) on chromosomal puffing, imaginal disc proliferation and pupariation in larvae of Drosophila melanogaster [11].
  • Among the synthesized compounds, a 6-membered cyclic hydrazine bearing two benzoyl groups (5) exists in three conformational states in solution, and the major unsymmetrical conformer of 5 is similar to that of RH-5849 on the basis of 1H NMR and X-ray analyses [12].
 

Gene context of RH 5849

  • The non-steroidal ecdysone agonist RH 5849 (1,2-dibenzoyl-1-tert-butylhydrazine) was found to inhibit in a dose-response and apparently competitive fashion the cytochrome P-450 dependent ecdysone 20-monooxygenase activity in the midgut of wandering stage last instar larvae of the tobacco hornworn, Manduca sexta [13].
 

Analytical, diagnostic and therapeutic context of RH 5849

  • When RH-5849 was introduced inside the axon and internal perfusion was halted, IK increased within a few minutes to the control level, indicating that the compound diffused freely through the membrane and bound to a receptor within the plane of the membrane [8].

References

  1. Acute toxicity and genotoxicity of two novel pesticides on amphibian, Rana N. Hallowell. Feng, S., Kong, Z., Wang, X., Zhao, L., Peng, P. Chemosphere (2004) [Pubmed]
  2. RH 5849, a nonsteroidal ecdysone agonist: effects on a Drosophila cell line. Wing, K.D. Science (1988) [Pubmed]
  3. Induction of enzymes involved in molting hormone (ecdysteroid) inactivation by ecdysteroids and an agonist, 1,2-dibenzoyl-1-tert-butylhydrazine (RH-5849). Williams, D.R., Chen, J.H., Fisher, M.J., Rees, H.H. J. Biol. Chem. (1997) [Pubmed]
  4. Characterization of ecdysteroid 26-hydroxylase: an enzyme involved in molting hormone inactivation. Williams, D.R., Fisher, M.J., Rees, H.H. Arch. Biochem. Biophys. (2000) [Pubmed]
  5. Comparative toxicity and ecdysone receptor affinity of non-steroidal ecdysone agonists and 20-hydroxyecdysone in Chironomus tentans. Smagghe, G., Dhadialla, T.S., Lezzi, M. Insect Biochem. Mol. Biol. (2002) [Pubmed]
  6. RH-5849, a nonsteroidal ecdysone agonist, does not mimic makisterone-A in Dysdercus koenigii. Koul, O., Kapil, R.S. Experientia (1994) [Pubmed]
  7. Assessing the genotoxicity of imidacloprid and RH-5849 in human peripheral blood lymphocytes in vitro with comet assay and cytogenetic tests. Feng, S., Kong, Z., Wang, X., Peng, P., Zeng, E.Y. Ecotoxicol. Environ. Saf. (2005) [Pubmed]
  8. Block of neuronal voltage-dependent K+ channels by diacylhydrazine insecticides. Salgado, V.L. Neurotoxicology (1998) [Pubmed]
  9. Effectiveness of the non-steroidal ecdysone mimic, RH-5849 for the control of Musca domestica vicina. Ghoneim, K.S., Fouda, M.A., Bream, A.S. Journal of the Egyptian Society of Parasitology. (1991) [Pubmed]
  10. In vitro effect of nonsteroidal ecdysone agonist RH 5849 on fat body acid phosphatase activity in rice moth, Corcyra cephalonica (Insecta). Ashok, M., Dutta-Gupta, A. Biochem. Int. (1991) [Pubmed]
  11. Effect of bisacylhydrazine ecdysteroid mimics (RH-5849 and RH-5992) on chromosomal puffing, imaginal disc proliferation and pupariation in larvae of Drosophila melanogaster. Farkas, R., Sláma, K. Insect Biochem. Mol. Biol. (1999) [Pubmed]
  12. Cyclic dibenzoylhydrazines reproducing the conformation of ecdysone agonists, RH-5849. Toya, T., Yamaguchi, K., Endo, Y. Bioorg. Med. Chem. (2002) [Pubmed]
  13. Regulation of cytochrome P-450 dependent steroid hydroxylase activity in Manduca sexta: effects of the ecdysone agonist RH 5849 on ecdysone 20-monooxygenase activity. Keogh, D.P., Smith, S.L. Biochem. Biophys. Res. Commun. (1991) [Pubmed]
 
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